Trimethyltetrathiafulvalene bearing an N-methylpyridinium substituent: Synthesis, crystal structures, and charge transfer properties

Adrian J. Moore, Andrei S. Batsanov, Martin R. Bryce, Judith A.K. Howard, Vladimir Khodorkovsky, Lev Shapiro, Alex Shames

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

The synthesis of 4,4′,5-trimethyl-5′-(4-pyridyl)tetrathiafulvalene (3), has been accomplished by reaction of the stannylated precursor 2 with 4-bromopyridine. Alkylation of 3 affords the N-methylpyridinium salt 4 which displays intramolecular charge transfer properties in solution as deduced from UV/Vis spectra, cyclic voltammetric data, and semiempirical quantum mechanical calculations. The X-ray crystal structures of neutral molecule 3, the salt (4+)I- and the charge transfer salt (4+)2(TCNQ3)2-. are reported. The positive charge in (4+)I- and (4+)2(TCNQ3)2-. is predominantly confined on the pyridinium ring. The structure of (4+)2(TCNQ3)2-. comprises segregated stacks of cations and TCNQ radical anions, with the anions overlapping in the usual ring-over-bond fashion. This salt is a semiconductor (σrt= 10-2 S cm-1).

Original languageEnglish
Pages (from-to)73-78
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number1
DOIs
StatePublished - 1 Jan 2001

Keywords

  • Charge-transfer
  • Crystal structures
  • Electron donors
  • Tetracyano-p-quinodimethane
  • Tetrathiafulvalenes

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